You never forget your first Nigerian Prince. From the desk of a barrister named Art Vandewald, His Royal Highness himself has sent you, of all people, a distress e-mail, urging you to send help in the form of a nominal bank wire. You’re his last and only hope, and in return for that kindness, he’ll reward you handsomely… when he surely gets out of his temporary bind.

In the early days of the Internet, hapless princes all seemed to have secret fortunes, but the Nigerian variant was the wealthiest and most generous of all. Of course, he was nothing more than the latest incarnation of a century’s old scam, one that had circled the world and back, but he was effective because he preyed on one of our greatest weaknesses: greed.

But he’s losing his charms.

The technology that once brought him to life is now thwarting his distress messages, but more importantly, we’ve simply grown tired of him — he always asking for favors. So con artists are adapting the beloved Prince to infiltrate our most intimate social circles. It’s Spam 2.0: the Prince is getting a makeover.

Spam Through the Ages

Last spring, digital spam turned 35-years-old. In 1978, Gary Thuerk, then a marketing manager at Digital Equipment Corp., sent a mass e-mail to the 400 members of ARPAnet, the first major wide-area computer network, according to a 2007 Computer World interview with Thuerk. Instead of sending separate messages, which was the custom then, he blasted out one copy — an advertisement for his computers — to them all. With one swift click of the mouse, he was crowned the father of spam.

“Actually, I think of myself as the father of e-marketing — there’s a difference,” he told Computer World. “We wanted to reach as many as people as possible to let them know about our new product.”

The backlash was swift. Recipients complained and an ARPAnet representative called him up and “chewed” him out. “The best complaint came from a guy at the University of Utah,” Thuerk said in the interview. “He said when he got in the office in the morning he couldn’t use his computer — the spam had used up all his company’s disk space.”

But the marketing tactic worked. With just one e-mail, he drummed over $13 million worth of DEC machines sales.

The concept of spam started before cursors flickered on computer screens. As the U.S. Civil War was drawing to a close, Western Union let customers pay more to send telegrams to multiple recipients. And from 1864 until the Great Depression, couriers often hand-delivered yellow envelopes, containing high-brow yet vague “investment offers,” to wealthy North Americans.

The word “spam” is actually an acronym for “Supply Processed American Meat.” As a food staple among soldiers during World War 2, the canned luncheon meat gained mass appeal among the British lower class due to its cheap cost and long shelf life. In the ’70s, the term became a buzzword for low-quality fodder when comedy troupe Monty Python created a sketch about a cafe that served Spam with every dish.

In 1988, fraudsters, looking for ways to pry hard-earned cash from unsuspecting netizens, modeled spam after chain letters and “get rich quick” schemes, forever linking the mystery meat with unsolicited e-mail. But it didn’t become mainstream until the ’90s, when a shadowy figure popped up in inboxes around the world: the Nigerian Prince.

Millions of e-mails asked for a few thousand dollars to help secure the release of a beloved royal, promising a ten-fold return. But in inner circles, it was just an old scheme with a new face, called the “advanced-fee scam,” or simply a 419, which comes from the antifraud section of Nigeria‘s criminal code.

“The advance-fee scam seems perfectly made for the medium of the Internet, with its anonymity and ability to send thousands of e-mails with a single keystroke,” Finn Brunton, an assistant professor at University of Michigan‘s School of Information and author of the book, “Spam: A Shadow History of the Internet,” told the Boston Globe.

The Nigerian Prince used the same basic premise as the “Spanish Prisoner” scam from 400 years back: a Marquis in the French Revolution, a soldier in the Spanish-American War or our Nigerian friend in modern times asks for a small wire. Then, in exchange for your kindness, he promises to give you a piece of his fortune, in the form of frozen bank accounts, Cuban gold or gems buried on a Parisian estate.

The cons work because deep down, we’re greedy. We also believe that where there’s turmoil — during a revolution or war or, in the case of Nigeria, a country whose government is up for grabs — people can make out like bandits. And maybe, this one time, it can be us.

“There would be no 419 scam if there are no greedy, credulous and criminally-minded victims ready to reap where they did not sow,” a spokesman for the Nigerian Embassy in Washington said back in 2003.

But once you take the bait, of course, unexpected delays start popping up, problems that need you to send more money to solve. “The longer you play along, the more you fall prey to what economists call the ‘sunk cost fallacy’,” Brunton said. “You’ve already put so much money in that it seems crazy to turn back now.”

An elderly couple in Tampa, Fla. found out the hard way. After sending what started as a small sum of money, they were strung along, wiring more and more before eventually mortgaging their house and losing over $350,000. According to the U.S. Internet Crime Complaint Center, nearly 28,000 advance-fee scams were filed with law enforcement in 2011, making it the third most frequent type of online crime in the U.S. In 2012, scammers used the Internet defrauded thousands of victims out of an estimated $525 million, an eight percent rise from just a year ago.

Spam is a numbers game: blanket a huge number of people and a few responses make it worth the effort. With e-mail, it’s easy to hit a large volume of targets cheaply, and that’s why spammers, once a novelty, became a major annoyance.

Legions of countermeasures have tried to fight the mountain of princely pleas. First-generation filters, for example, looked for and calculated certain word combinations to flag unsolicited e-mails. But in the cat-and-mouse game, spammers evolved, adding misspellings, famous names and often tacky graphics to bypass filters. That’s why you see the number “0” instead of the letter “o,” or “free mortgage quotes” as “free m0rtgage qu0tes.”

Of course, filters became smarter too, stemming the rising tide of spam, and by 2012, unsolicited e-mails plummeted to 30 billion messages a day, down from 42 billion a year earlier, according to Internet security firm Symantec. But scammers are transitioning to social media, hoping to lure clicks, spread viruses and grab personal information.

And new platforms, it seems, demand a new gambit.

Spammers love social media because it offers two things e-mails cannot: trust and sharing. When you get a message from a friend, you’re more likely to click on it, and that gives them access to birthdays, home addresses and even interests — data they’d never over e-mail. Vine, Twitter’s six-second video sharing service, for example, launched to great fanfare, boasting over 13 million users in a little under half a year. But just as users flocked to it, so did spam bots, posting comments directing you to external scam sites.

Good Night Sweet Prince, Hello Acacia

The Nigerian Prince’s next guise is an imaginary friend — someone you know or want to know. Being a royal is passe, and to go viral, you need a more appealing, relatable figure — one that posts pictures, sends tweets and generally exists like a real person.

A popular online persona has power, and not just in attracting links, clicks and purchases. Teenage social maven Acacia Brinley, for example, sent thousands of her then-120,000 followers to Pheed, a social media platform, with a simple tweet. The response propelled the fledgling site to become one of most-downloaded apps in Apple’s Store that week.

Brinley is just a normal Southern Californian girl, but she represents the powerful influence of social media. And the next generation of spammers are creating entire networks of “bots” that look, sound and interact like real people, Joseph Turian, a former data scientist at the University of Montreal, said at a big data conference covered by the tech blog Gigaom. Turian, who founded MetaOptimize, which studies the impact of artificial influence manipulation, said the spammers are analyzing language to learn to compose messages that look less like a program wrote them and more like a stupid human.

Right now, the aim is to bypass filters, but with the help of self-learning algorithms, bots are growing smarter with each passing day. And in the near future, fraudsters will be able to create hundreds of thousands of accounts so life-like that you can’t tell them apart from Brinley.

And if you think you’re smart enough to see through the gambit, think again.

Spammers are already finding success on social media. In 2009, Twitterclassified nine percent of all messages as spam. And according to Lutz Finger, co-founder of Fisheye Analytics, about seven percent of all followers are actually bots.

Who hasn’t received a friend request from an attractive stranger?

Studies show four-in-five of us received those unwanted requests and messages, and nearly 20 percent accept them into our private lives. When we do, those programs kick in, starting conversations so enticing that they trick about one-in-three of us, even after we’re warned.

Today, nearly half of all Americans get their news online, topping newspapers and radio, according to a Pew Research study. And those articles, written by reporters, are often sourced from social media, using tools that scour Twitter for real-time information. In fact, Finger said over half of journalists say they trust social media.

That’s a real threat. As the next generation of spam becomes increasingly sophisticated, con artists will attempt to influence consumer choice and public opinion, like sell phony goods, push brands or even affect election results. But in that cat-and-mouse game, data scientists are developing security measures to deter social media bots. It’s an ongoing war. And if you thought the Nigerian Prince was a hassle, just wait until he unmasks his next scheme.

The original version of this article included quotes or statements that were not clearly attributed to the original sources.